A retrospective on work at Big Tech, agencies and startups

Disclaimer: Everything written here is my personal opinion only, and is no way a reflection of the opinion of any of my employers, past or present.

I’ve been a professional designer for about 10 years, mostly in tech. I’ve split my time between different work contexts: agencies, startups, and big tech — with some freelance in between. I have colleagues with similarly varied experiences, and we often speak of the differences between these models of working. After many conversations during my three years at Google, I decided to write down some observations that seemed to resonate among us.

To my surprise, my experience at Google is somewhat more reminiscent of my time in agencies, compared with my time at startups. I think this has something to do with the adaptability required to work across different client projects (agency), or to work with thousands of colleagues on products used by billions of people (Google).

But which one is best?

There is no “right” way to work, but keep reading for some more specific observations. In the end, there are people, problems and structures — the more our structures respond to people and problems, the better. Beware any place that claims to have their process totally figured out.

Of course I’m not the only one who’s written about this: There are articles from designers starting their career, and from seasoned leaders. There’s also a lot of tips on how to get jobs at places like Google, including this video by my super talented colleague. If you want my advice, you can jump to the bottom of the article.

But here are my observations, as someone who has worked at agencies and startups and now works in Big Tech:

Want to know what I mean by any of that? Well…

I’ve worked at jobs where I wasn’t very good at what I did. And I’ve worked with people who were not experts in their role either. If you’re a Normal Human Being, you’ve probably been in both those positions, too. If you work at a Normal Company you’ll probably meet people along a spectrum of skills and aptitude.

But at Google, everyone I’ve met is very good at what they do. Even junior designers early in their career. I sometimes find this really intimidating (“imposter syndrome”), but do my best to convince myself that I, too, must be one of these people who are good at what they do.

If you’re confident in yourself and have a growth mindset, you’ll find yourself with a great opportunity to learn and feel inspired to do your best work.

But if you’re insecure about your own skills and find yourself prone to jealousy or harsh self-criticism, you may feel overwhelmed and struggle.

Or If you’re a Normal Human Being like me, you’ll feel both.

Not the most romantic topic, but the money in Big Tech is pretty good. The compensation structure can be confusing if you’re used to only evaluating salaries (like I was). When interviewing at Big Tech you need to look at your “total comp,” of which your salary is just one part.

I love what I do but I work at a job to support myself and my family, and these big tech firms do a good job of that. My experience is that agencies pay the least — and often ask the most. Startups sometimes have higher salaries and often stock options, but buying into it may be a gamble. Of course, in theory, that gamble can pay off big time and you could end up with millions after a successful IPO, but that’s also obviously not the most common scenario.

Most organizations have some kind of performance review system, but based on my experience and conversations with peers, the process in Big Tech is comparatively rigorous. You must prove that you had impact and your manager and peers must vouch for you with evidence. The process takes up a great deal of time and emotional energy, particularly for managers. By the end of it you finish with a “grade.”

The process of getting this grade is a fundamental part of life across Big Tech. The focus of these evaluations is the impact you had on your projects as an individual – not just the quality of your work. This took time to wrap my head around: it wasn’t really my design work being evaluated so much as my ability to actually influence the product, team and business in the right direction.

Before Google, every place I’ve worked for had some way to evaluate your performance — generally a combination of manager and peer feedback. The processes were often ad-hoc: I certainly received helpful feedback, but I also got off-the-cuff personal opinions and sometimes no feedback at all.

If you loved getting good grades in school, and have always been motivated by high test scores and enrollment in competitive institutions, then you will feel at home in Big Tech. If you hate the idea of being formally evaluated regularly (and rigorously), it can be a tough environment. It’s not my favorite part of life here, but I’d take it over the ambiguity that crops up in many other places. Often, that ambiguity can lead to evaluations and promotions based on a combination of personality, the perceived chance of you leaving, your friendship with management, or how forcefully you’ve pushed. This doesn’t always make for an inspiring environment to grow into.

My experience (and those of my colleagues) is that at startups, your work and maybe even identity center around your cross-functional product team. Designers looked to each other for support and tips, but the work and rituals that guided your ux-eng-PM group was the center of your experience.

Traditional or large agencies may also often strong rituals and structures, but functions are more siloed – a designer will spend a lot of time with other designers. For better or worse, that siloing seems to be phasing out, with some modern agencies creating teams made up of design, research and engineering.

Google is a big company made up of many departments, many of which work differently. But my experience is that your function (in my case, UX Design) is your primary identity. I still work with a cross-functional group, but most of my time is working with designers, design tools, design reviews, design research, etc. Being under the eye of so many designers can be exhausting, although it has forced me to button up my craft and presentation skills. Cross-functional teams meet regularly, but rarely have the routines of orgs that use Agile, Scrum, or other capital-letter project management methodologies.

At first, I found this working model a little alienating. Without the rituals of a tight-knit working group, it felt like I was on my own. But I built relationships over time, and now feel a greater sense of independence and self-management than I did anywhere else I worked. Not what I expected when I joined such a big company!

Getting things done can be hard anywhere. But even with all of these smart people, it can still be challenging to get things done at such a big company. But why?

Scale: Many of Google’s products touch billions of people across the world and work on a wide array of devices. Creating even a simple features that works in all of those contexts is complex and therefore time-consuming.

Alignment: There are a lot of teams, products and people at Google. Because of the scale of both the user base and the company, projects require working with many teams and people. Even when everyone is aligned, getting timing and details right is still hard. And of course getting that alignment in the first place could be a challenge.

The best explanation I’ve heard of this complex system is @komoroseke’s collaboration headwinds presentation, who even provides some math to help us understand this complexity. For example, a project with 10 people, each 90% likely to succeed in their tasks, makes the project as a whole about 35% likely to succeed. An oversimplification maybe — but a useful one.

Startups, by definition, don’t operate at the same scale as Big Tech, which in turn reduces some of the alignment challenges. Many teams are happy to just get anything that works out the door and have limited interdependencies. Alignment can still be challenging, but is generally more manageable: most decisions can be made at a small team level, and while disagreement can end up feeling more personal, it is not a defining theme of life at these smaller firms.

In agencies, getting (design) “work” done is generally not a challenge. Scale and alignment are still issues but the sources are different. The scale and scope of work I had to manage in a given week was intense, and getting alignment between clients, account managers, and tech leads could sometimes feel like a herculean effort.

My favorite part of working at Google is that even when some of our day to day work can feel “small” (remember small feature * billions of people = hard), we are asked to think big. Even if your project is going to take over a year, leaders will want to know what’s next. And what’s next after that. And why. If you share a compelling vision, you may get more resources (and pressure) to produce even more amazing work. The back and forth between vision and iterative work is challenging, but is one of the more rewarding aspects of the job.

At startups, you can’t take the future for granted so there is more focus on the present. Ship as much as possible, at the highest quality possible given today’s constraints. If you were to go heads down for 6 weeks and come back with 1 week’s worth of iterative work and 5 weeks of future thinking, most people would say you’re not doing your job. In contrast, that is your job at Google.

At a good agency, you’ll also think big and work small, but more linearly. In the pitch or early parts of a project you may be asked to craft grand visions, and then afterwards get into the nitty gritty. Unfortunately, a common scenario is that agencies split these tasks between people: some work on visioning pitches while others work on executing and managing the project. It’s tough because naturally most people tend to be better at one of these areas than the other, so splitting the work that way makes some sense. But it’s also a disservice to both individual growth and to the actual work itself, both of which can become stale via this handoff process.

My best advice would be to try lots of different work environments. You’ll learn more about yourself, people, and the industry you work in. If I could go back in time and design the right order to do these things, for me it might look something like:

But really, the one thing that matters is that you try different things, and do what you think is best for you.